• Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • Along Came the Mistress

Along Came the Mistress

The next morning at work, I just couldn't concentrate. People were lining out the door as we rushed around, cleaning and serving, but I just couldn't get Gabrielle out of my head. Her beautiful body, her passionate moans or her expression of joy as she sucked clean her cum coated fingers in front of me.

Once the rush ended, I went through to the back and checked my phone, but my heart sank with disappointment as I discovered my inbox was empty.

She didn't come into the shop either and as I went home that evening, I started to wonder, had it just been a onetime thing?

But as I arrived home, my phone lit up with Gabrielle's number. I felt my spirits among other things rise as I opened the message but what awaited me was far from what I was expecting.

"Hello, Sir, I believe you got very acquainted my little slut last night and I don't approve. She knew she had to talk to me first, so I wonder...what makes you so special? Tomorrow, I'll be coming into your work to find out. From, The Mistress."

As I read the message several times over, I felt fear begin to set in. This wasn't what I had expected and in my head, I had a mental image of some muscular woman coming into my work and slamming my head against the counter.

"God. I really need to stop my imagination." I try to tell myself, but the worries still hit me hard.

That night, I didn't get any sleep. My mind kept wandering to Gabrielle, possibly being punished for falling in love with a guy like me.

Walking into work the next day, I felt on edge, constantly looking over my shoulder and jumping when women walked in the door.

But that's when it happened.

Gabrielle walked in, her flowing dress and blond hair looking so radiant that I nearly dropped a tray of dishes and next to her was a new woman just a little taller than her.

The new woman had curves and then some. Her breasts had to be at least E cup and they were barely contained by her tight top. She moved a lock of her long chestnut hair from her face and smirked as she saw me looking.

"Well hello sir. Glad, we could finally meet." The new girl says, putting emphasis on sir. Gabrielle just stood there blushing and fiddling with her fingers.

"So, you're the mistress?" I ask nervously, lowering my voice a little but she smirks and begins to laugh.

"You got it. Now then, Gabrielle here tells me that she wants to leave my...protection and be with the...How did she put it? Man, of her dreams?" She asks, making Gabrielle blush even harder and lowering her head in embarrassment.

The mistress laughs at this as I look to Gabrielle, my own cheeks blushing deeper at those words.

They both take a seat and after talking with my manager, I go on my break, sitting opposite them.

"So, what do you want?" I ask her, unsure what else to say.

The mistress smirks as she leans over the table, the top of her large breasts on display. "I want you to prove yourself." She says before leaning back, a wide grin on her face.

"How?" I ask, realising that I am completely at her mercy right now.

She gives Gabrielle a nudge and she slides over, sitting on my lap but it's a few seconds before I feel a soft buzzing against my leg.

Noticing my expression, Gabrielle blushes. "I...felt so...empty after you fucked me. But nothing is the same as you." She says, placing my hand on her leg.

"You want to know how to prove yourself? Follow us and we'll show you." She says as the two of them get up and head to the door and without a second thought, I followed.

She led us into the disabled toilets and locked the door behind us as she pulled her top off over her head, her breast fully exposed.

"I want you to make me cum. If you can do that, I'll let you have Gabrielle." She says as she finishes undressing.

I look at Gabrielle and she is looking like she wants to say something but doesn't dare.

"So, what are we waiting for? Show me the cock you made Gabrielle into a woman with." She says as she sits on the seat, spreads her legs and slowly starts to play with her pussy.

I feel torn as I watch this. My cock wants to fuck the mistress hard but my heart loves Gabrielle.

Gabrielle finally snaps and a tear runs down her cheek. "Please stop this Melanie...I mean, mistress." She says, begging for Melanie to stop.

Melanie looks at her and smirks. "Oh? Is my little sister getting jealous? Don't worry, I was only testing him." She says, standing up and walking over. "But I bet you want to do it." She says as she pulls Gabrielle's dress up, revealing a small bulge in the back of her panties, slowly vibrating.

She tries to cover it, but I finally can't take it and pull Gabrielle into a deep kiss. "I'm sorry, I can't help myself anymore." I say but she shakes her head as she kisses back. "No, I wanted you too." She says as she presses herself against me, her clitty straining against her panties.

I smirk as I slide a hand down, rubbing her clitty and pulling it back up, my fingers coated in her sissy cum. "Mmmm, someone's getting very excited." I say but before I can do anything, she engulfs my fingers, sucking her own cum off.

"Good girl." I whisper in her ear as I undo my trousers, my cock springing out into the open. I spot Melanie's eyes widen and grin.

Gabrielle drops immediately to her knees, mouth open as she looks up into my eyes, begging for my to fill her mouth again and I oblige.

I slowly slide my cock past her lips and into her wet mouth, her moan of pleasure dripping with lust and desire.

I run my hands through her hair as she starts to suck my cock, her mouth feeling even better than last time as she cradles my balls with the other.

Melanie walks over, smirking at the sight. "Mmmmm, tell me, how does my sister's mouth feel? Do you love it? Do you want to fill it with hot cum?" She asks, turning the mood up with dirty talk.

She kneels next to Gabrielle and kisses her cheek. "Sorry sis, but I can't let you have all the fun." She says as she leans under me and starts licking my balls, teasing my cum filled orbs with her soft tongue.

I groan deeply and thrust my hips, starting to fuck my way deeper into Gabrielle's throat. She doesn't resist and seems to enjoy having her man's cock in her mouth.

I soon pull out and smirk as I lie on the floor. "Mount my cock Gabrielle." I say and with an expression of pure bliss, she slides her panties to one side, pulls out the buzzing vibrator and slams down, moaning like a bitch in heat.

"Oh fuck, I've missed your cock. It's so...so good." She moans as she starts to rock her hips back and forth, grinding my cock even deeper inside herself, her pussy stretched around my cock.

Melanie smirks as she lowers herself onto my face, her pussy pressed against my mouth. "Mmmmm, please make me feel good too lover." She says as I realise I have no choice and flick my tongue over her pussy lips.

Fucking my baby and eating out her sister, I felt myself getting close to cumming as the two began to kiss passionately as they both rode me.

Without warning, I shoot my load into Gabrielle, her face lighting up and her eyes rolling back slightly in bliss as she lets out a silent moan, her body convulsing as she cums in her little panties.

Melanie frowns as she stands, leaving me with a mouth covered in her juices. "I didn't get to cum." She says before beginning to pull on her clothes but myself and Gabrielle look at one another and pull each other into a passionate kiss.

Little did we know that someone was stood outside the door, dress furled up as they fingered themselves.

*

(Thanks again for reading, I was nervous about how this one will turn out but thank you to Rustygh, your comment helped me continue.

Will the main character be able to keep Gabrielle? And who is the person watching them? You'll have to wait and find out. ;))

  • Index
  • /
  • Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • Along Came the Mistress

All contents © Copyright 1996-2023. Literotica is a registered trademark.

Desktop versionT.O.S.PrivacyReport a ProblemSupport

Version ⁨1.0.2+795cd7d.adb84bd⁩

We are testing a new version of this page. It was made in 450 milliseconds